Photophysical properties of benzanthrone derivatives: effect of substituent, solvent polarity and hydrogen bonding

Abstract Benzanthrone derivatives are potential fluorescent probes for various chemical and biological environments. A mechanistic understanding of their photophysical properties is pivotal for designing an efficient fluorescence sensor based on the benzanthrone framework. In this study, we report o...
Ausführliche Beschreibung

Gespeichert in:

Autor*in:	Siddlingeshwar, B. [verfasserIn] Kirilova, Elena M. [verfasserIn] Belyakov, Sergey V. [verfasserIn] Divakar, Darshan Devang [verfasserIn] Alkheraif, Abdulaziz Abdullah [verfasserIn]

Format:	E-Artikel
Sprache:	Englisch

Erschienen:	2018

Übergeordnetes Werk:	Enthalten in: Photochemical & photobiological sciences - Heidelberg : Springer, 2002, 17(2018), 4 vom: Apr., Seite 453-464
Übergeordnetes Werk:	volume:17 ; year:2018 ; number:4 ; month:04 ; pages:453-464

Links:	Volltext

DOI / URN:	10.1039/c7pp00392g

Katalog-ID:	SPR043731139

Internformat


LEADER	01000caa a22002652 4500
001	SPR043731139
003	DE-627
005	20220112055016.0
007	cr uuu---uuuuu
008	210409s2018 xx \|\|\|\|\|o 00\| \|\|eng c
024	7		\|a 10.1039/c7pp00392g \|2 doi
035			\|a (DE-627)SPR043731139
035			\|a (DE-599)SPRc7pp00392g-e
035			\|a (SPR)c7pp00392g-e
040			\|a DE-627 \|b ger \|c DE-627 \|e rakwb
041			\|a eng
082	0	4	\|a 620 \|q ASE
084			\|a 35.16 \|2 bkl
084			\|a 42.14 \|2 bkl
100	1		\|a Siddlingeshwar, B. \|e verfasserin \|4 aut
245	1	0	\|a Photophysical properties of benzanthrone derivatives: effect of substituent, solvent polarity and hydrogen bonding
264		1	\|c 2018
336			\|a Text \|b txt \|2 rdacontent
337			\|a Computermedien \|b c \|2 rdamedia
338			\|a Online-Ressource \|b cr \|2 rdacarrier
520			\|a Abstract Benzanthrone derivatives are potential fluorescent probes for various chemical and biological environments. A mechanistic understanding of their photophysical properties is pivotal for designing an efficient fluorescence sensor based on the benzanthrone framework. In this study, we report on the effect of chemical substitution on the photophysical properties of two benzanthrone derivatives, namely, 3-(N′-methyl)-piperazino-7H-benzo[de]anthracen-7-one [Me-PBA] and 3-(N′-phenyl)-piperazino-7H-benzo[de]anthracen-7-one [Ph-PBA] in different solvents and solvent mixtures of varying polarities and proticities. Both benzanthrone derivatives show interesting solvent-dependent photophysical properties. Although both derivatives exhibit strong intramolecular charge transfer (ICT) characteristics in the excited state, the extent of the charge transfer is significantly influenced by the nature of the chemical substitution. Modulation of photophysical parameters as a function of solvent properties led us to propose that ICT is affected by solvent polarity and hydrogen bonding. From the viscosity effect, it is revealed that the weaker emission of Ph-PBA compared to Me-PBA in polar solvents is primarily due to the non-radiative torsional motion of the phenyl group in the former derivative. In protic solvents, intermolecular hydrogen bonding imparts strong non-radiative deactivation to both derivatives, thus rendering a weak fluorescence yield.
700	1		\|a Kirilova, Elena M. \|e verfasserin \|4 aut
700	1		\|a Belyakov, Sergey V. \|e verfasserin \|4 aut
700	1		\|a Divakar, Darshan Devang \|e verfasserin \|4 aut
700	1		\|a Alkheraif, Abdulaziz Abdullah \|e verfasserin \|4 aut
773	0	8	\|i Enthalten in \|t Photochemical & photobiological sciences \|d Heidelberg : Springer, 2002 \|g 17(2018), 4 vom: Apr., Seite 453-464 \|w (DE-627)342893742 \|w (DE-600)2072584-X \|x 1474-9092 \|7 nnns
773	1	8	\|g volume:17 \|g year:2018 \|g number:4 \|g month:04 \|g pages:453-464
856	4	0	\|u https://dx.doi.org/10.1039/c7pp00392g \|z lizenzpflichtig \|3 Volltext
912			\|a GBV_USEFLAG_A
912			\|a SYSFLAG_A
912			\|a GBV_SPRINGER
912			\|a GBV_ILN_24
912			\|a GBV_ILN_32
912			\|a GBV_ILN_62
912			\|a GBV_ILN_69
912			\|a GBV_ILN_74
912			\|a GBV_ILN_120
912			\|a GBV_ILN_170
912			\|a GBV_ILN_374
912			\|a GBV_ILN_702
912			\|a GBV_ILN_2020
912			\|a GBV_ILN_2021
912			\|a GBV_ILN_2026
912			\|a GBV_ILN_2027
912			\|a GBV_ILN_2110
912			\|a GBV_ILN_2190
912			\|a GBV_ILN_4035
912			\|a GBV_ILN_4037
912			\|a GBV_ILN_4112
912			\|a GBV_ILN_4305
936	b	k	\|a 35.16 \|q ASE
936	b	k	\|a 42.14 \|q ASE
951			\|a AR
952			\|d 17 \|j 2018 \|e 4 \|c 04 \|h 453-464

Indexfelder

author_variant	b s bs e m k em emk s v b sv svb d d d dd ddd a a a aa aaa
matchkey_str	article:14749092:2018----::htpyiapoeteobnatrndrvtvsfetfusiunslet
hierarchy_sort_str	2018
bklnumber	35.16 42.14
publishDate	2018
allfields	10.1039/c7pp00392g doi (DE-627)SPR043731139 (DE-599)SPRc7pp00392g-e (SPR)c7pp00392g-e DE-627 ger DE-627 rakwb eng 620 ASE 35.16 bkl 42.14 bkl Siddlingeshwar, B. verfasserin aut Photophysical properties of benzanthrone derivatives: effect of substituent, solvent polarity and hydrogen bonding 2018 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier Abstract Benzanthrone derivatives are potential fluorescent probes for various chemical and biological environments. A mechanistic understanding of their photophysical properties is pivotal for designing an efficient fluorescence sensor based on the benzanthrone framework. In this study, we report on the effect of chemical substitution on the photophysical properties of two benzanthrone derivatives, namely, 3-(N′-methyl)-piperazino-7H-benzo[de]anthracen-7-one [Me-PBA] and 3-(N′-phenyl)-piperazino-7H-benzo[de]anthracen-7-one [Ph-PBA] in different solvents and solvent mixtures of varying polarities and proticities. Both benzanthrone derivatives show interesting solvent-dependent photophysical properties. Although both derivatives exhibit strong intramolecular charge transfer (ICT) characteristics in the excited state, the extent of the charge transfer is significantly influenced by the nature of the chemical substitution. Modulation of photophysical parameters as a function of solvent properties led us to propose that ICT is affected by solvent polarity and hydrogen bonding. From the viscosity effect, it is revealed that the weaker emission of Ph-PBA compared to Me-PBA in polar solvents is primarily due to the non-radiative torsional motion of the phenyl group in the former derivative. In protic solvents, intermolecular hydrogen bonding imparts strong non-radiative deactivation to both derivatives, thus rendering a weak fluorescence yield. Kirilova, Elena M. verfasserin aut Belyakov, Sergey V. verfasserin aut Divakar, Darshan Devang verfasserin aut Alkheraif, Abdulaziz Abdullah verfasserin aut Enthalten in Photochemical & photobiological sciences Heidelberg : Springer, 2002 17(2018), 4 vom: Apr., Seite 453-464 (DE-627)342893742 (DE-600)2072584-X 1474-9092 nnns volume:17 year:2018 number:4 month:04 pages:453-464 https://dx.doi.org/10.1039/c7pp00392g lizenzpflichtig Volltext GBV_USEFLAG_A SYSFLAG_A GBV_SPRINGER GBV_ILN_24 GBV_ILN_32 GBV_ILN_62 GBV_ILN_69 GBV_ILN_74 GBV_ILN_120 GBV_ILN_170 GBV_ILN_374 GBV_ILN_702 GBV_ILN_2020 GBV_ILN_2021 GBV_ILN_2026 GBV_ILN_2027 GBV_ILN_2110 GBV_ILN_2190 GBV_ILN_4035 GBV_ILN_4037 GBV_ILN_4112 GBV_ILN_4305 35.16 ASE 42.14 ASE AR 17 2018 4 04 453-464
spelling	10.1039/c7pp00392g doi (DE-627)SPR043731139 (DE-599)SPRc7pp00392g-e (SPR)c7pp00392g-e DE-627 ger DE-627 rakwb eng 620 ASE 35.16 bkl 42.14 bkl Siddlingeshwar, B. verfasserin aut Photophysical properties of benzanthrone derivatives: effect of substituent, solvent polarity and hydrogen bonding 2018 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier Abstract Benzanthrone derivatives are potential fluorescent probes for various chemical and biological environments. A mechanistic understanding of their photophysical properties is pivotal for designing an efficient fluorescence sensor based on the benzanthrone framework. In this study, we report on the effect of chemical substitution on the photophysical properties of two benzanthrone derivatives, namely, 3-(N′-methyl)-piperazino-7H-benzo[de]anthracen-7-one [Me-PBA] and 3-(N′-phenyl)-piperazino-7H-benzo[de]anthracen-7-one [Ph-PBA] in different solvents and solvent mixtures of varying polarities and proticities. Both benzanthrone derivatives show interesting solvent-dependent photophysical properties. Although both derivatives exhibit strong intramolecular charge transfer (ICT) characteristics in the excited state, the extent of the charge transfer is significantly influenced by the nature of the chemical substitution. Modulation of photophysical parameters as a function of solvent properties led us to propose that ICT is affected by solvent polarity and hydrogen bonding. From the viscosity effect, it is revealed that the weaker emission of Ph-PBA compared to Me-PBA in polar solvents is primarily due to the non-radiative torsional motion of the phenyl group in the former derivative. In protic solvents, intermolecular hydrogen bonding imparts strong non-radiative deactivation to both derivatives, thus rendering a weak fluorescence yield. Kirilova, Elena M. verfasserin aut Belyakov, Sergey V. verfasserin aut Divakar, Darshan Devang verfasserin aut Alkheraif, Abdulaziz Abdullah verfasserin aut Enthalten in Photochemical & photobiological sciences Heidelberg : Springer, 2002 17(2018), 4 vom: Apr., Seite 453-464 (DE-627)342893742 (DE-600)2072584-X 1474-9092 nnns volume:17 year:2018 number:4 month:04 pages:453-464 https://dx.doi.org/10.1039/c7pp00392g lizenzpflichtig Volltext GBV_USEFLAG_A SYSFLAG_A GBV_SPRINGER GBV_ILN_24 GBV_ILN_32 GBV_ILN_62 GBV_ILN_69 GBV_ILN_74 GBV_ILN_120 GBV_ILN_170 GBV_ILN_374 GBV_ILN_702 GBV_ILN_2020 GBV_ILN_2021 GBV_ILN_2026 GBV_ILN_2027 GBV_ILN_2110 GBV_ILN_2190 GBV_ILN_4035 GBV_ILN_4037 GBV_ILN_4112 GBV_ILN_4305 35.16 ASE 42.14 ASE AR 17 2018 4 04 453-464
allfields_unstemmed	10.1039/c7pp00392g doi (DE-627)SPR043731139 (DE-599)SPRc7pp00392g-e (SPR)c7pp00392g-e DE-627 ger DE-627 rakwb eng 620 ASE 35.16 bkl 42.14 bkl Siddlingeshwar, B. verfasserin aut Photophysical properties of benzanthrone derivatives: effect of substituent, solvent polarity and hydrogen bonding 2018 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier Abstract Benzanthrone derivatives are potential fluorescent probes for various chemical and biological environments. A mechanistic understanding of their photophysical properties is pivotal for designing an efficient fluorescence sensor based on the benzanthrone framework. In this study, we report on the effect of chemical substitution on the photophysical properties of two benzanthrone derivatives, namely, 3-(N′-methyl)-piperazino-7H-benzo[de]anthracen-7-one [Me-PBA] and 3-(N′-phenyl)-piperazino-7H-benzo[de]anthracen-7-one [Ph-PBA] in different solvents and solvent mixtures of varying polarities and proticities. Both benzanthrone derivatives show interesting solvent-dependent photophysical properties. Although both derivatives exhibit strong intramolecular charge transfer (ICT) characteristics in the excited state, the extent of the charge transfer is significantly influenced by the nature of the chemical substitution. Modulation of photophysical parameters as a function of solvent properties led us to propose that ICT is affected by solvent polarity and hydrogen bonding. From the viscosity effect, it is revealed that the weaker emission of Ph-PBA compared to Me-PBA in polar solvents is primarily due to the non-radiative torsional motion of the phenyl group in the former derivative. In protic solvents, intermolecular hydrogen bonding imparts strong non-radiative deactivation to both derivatives, thus rendering a weak fluorescence yield. Kirilova, Elena M. verfasserin aut Belyakov, Sergey V. verfasserin aut Divakar, Darshan Devang verfasserin aut Alkheraif, Abdulaziz Abdullah verfasserin aut Enthalten in Photochemical & photobiological sciences Heidelberg : Springer, 2002 17(2018), 4 vom: Apr., Seite 453-464 (DE-627)342893742 (DE-600)2072584-X 1474-9092 nnns volume:17 year:2018 number:4 month:04 pages:453-464 https://dx.doi.org/10.1039/c7pp00392g lizenzpflichtig Volltext GBV_USEFLAG_A SYSFLAG_A GBV_SPRINGER GBV_ILN_24 GBV_ILN_32 GBV_ILN_62 GBV_ILN_69 GBV_ILN_74 GBV_ILN_120 GBV_ILN_170 GBV_ILN_374 GBV_ILN_702 GBV_ILN_2020 GBV_ILN_2021 GBV_ILN_2026 GBV_ILN_2027 GBV_ILN_2110 GBV_ILN_2190 GBV_ILN_4035 GBV_ILN_4037 GBV_ILN_4112 GBV_ILN_4305 35.16 ASE 42.14 ASE AR 17 2018 4 04 453-464
allfieldsGer	10.1039/c7pp00392g doi (DE-627)SPR043731139 (DE-599)SPRc7pp00392g-e (SPR)c7pp00392g-e DE-627 ger DE-627 rakwb eng 620 ASE 35.16 bkl 42.14 bkl Siddlingeshwar, B. verfasserin aut Photophysical properties of benzanthrone derivatives: effect of substituent, solvent polarity and hydrogen bonding 2018 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier Abstract Benzanthrone derivatives are potential fluorescent probes for various chemical and biological environments. A mechanistic understanding of their photophysical properties is pivotal for designing an efficient fluorescence sensor based on the benzanthrone framework. In this study, we report on the effect of chemical substitution on the photophysical properties of two benzanthrone derivatives, namely, 3-(N′-methyl)-piperazino-7H-benzo[de]anthracen-7-one [Me-PBA] and 3-(N′-phenyl)-piperazino-7H-benzo[de]anthracen-7-one [Ph-PBA] in different solvents and solvent mixtures of varying polarities and proticities. Both benzanthrone derivatives show interesting solvent-dependent photophysical properties. Although both derivatives exhibit strong intramolecular charge transfer (ICT) characteristics in the excited state, the extent of the charge transfer is significantly influenced by the nature of the chemical substitution. Modulation of photophysical parameters as a function of solvent properties led us to propose that ICT is affected by solvent polarity and hydrogen bonding. From the viscosity effect, it is revealed that the weaker emission of Ph-PBA compared to Me-PBA in polar solvents is primarily due to the non-radiative torsional motion of the phenyl group in the former derivative. In protic solvents, intermolecular hydrogen bonding imparts strong non-radiative deactivation to both derivatives, thus rendering a weak fluorescence yield. Kirilova, Elena M. verfasserin aut Belyakov, Sergey V. verfasserin aut Divakar, Darshan Devang verfasserin aut Alkheraif, Abdulaziz Abdullah verfasserin aut Enthalten in Photochemical & photobiological sciences Heidelberg : Springer, 2002 17(2018), 4 vom: Apr., Seite 453-464 (DE-627)342893742 (DE-600)2072584-X 1474-9092 nnns volume:17 year:2018 number:4 month:04 pages:453-464 https://dx.doi.org/10.1039/c7pp00392g lizenzpflichtig Volltext GBV_USEFLAG_A SYSFLAG_A GBV_SPRINGER GBV_ILN_24 GBV_ILN_32 GBV_ILN_62 GBV_ILN_69 GBV_ILN_74 GBV_ILN_120 GBV_ILN_170 GBV_ILN_374 GBV_ILN_702 GBV_ILN_2020 GBV_ILN_2021 GBV_ILN_2026 GBV_ILN_2027 GBV_ILN_2110 GBV_ILN_2190 GBV_ILN_4035 GBV_ILN_4037 GBV_ILN_4112 GBV_ILN_4305 35.16 ASE 42.14 ASE AR 17 2018 4 04 453-464
allfieldsSound	10.1039/c7pp00392g doi (DE-627)SPR043731139 (DE-599)SPRc7pp00392g-e (SPR)c7pp00392g-e DE-627 ger DE-627 rakwb eng 620 ASE 35.16 bkl 42.14 bkl Siddlingeshwar, B. verfasserin aut Photophysical properties of benzanthrone derivatives: effect of substituent, solvent polarity and hydrogen bonding 2018 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier Abstract Benzanthrone derivatives are potential fluorescent probes for various chemical and biological environments. A mechanistic understanding of their photophysical properties is pivotal for designing an efficient fluorescence sensor based on the benzanthrone framework. In this study, we report on the effect of chemical substitution on the photophysical properties of two benzanthrone derivatives, namely, 3-(N′-methyl)-piperazino-7H-benzo[de]anthracen-7-one [Me-PBA] and 3-(N′-phenyl)-piperazino-7H-benzo[de]anthracen-7-one [Ph-PBA] in different solvents and solvent mixtures of varying polarities and proticities. Both benzanthrone derivatives show interesting solvent-dependent photophysical properties. Although both derivatives exhibit strong intramolecular charge transfer (ICT) characteristics in the excited state, the extent of the charge transfer is significantly influenced by the nature of the chemical substitution. Modulation of photophysical parameters as a function of solvent properties led us to propose that ICT is affected by solvent polarity and hydrogen bonding. From the viscosity effect, it is revealed that the weaker emission of Ph-PBA compared to Me-PBA in polar solvents is primarily due to the non-radiative torsional motion of the phenyl group in the former derivative. In protic solvents, intermolecular hydrogen bonding imparts strong non-radiative deactivation to both derivatives, thus rendering a weak fluorescence yield. Kirilova, Elena M. verfasserin aut Belyakov, Sergey V. verfasserin aut Divakar, Darshan Devang verfasserin aut Alkheraif, Abdulaziz Abdullah verfasserin aut Enthalten in Photochemical & photobiological sciences Heidelberg : Springer, 2002 17(2018), 4 vom: Apr., Seite 453-464 (DE-627)342893742 (DE-600)2072584-X 1474-9092 nnns volume:17 year:2018 number:4 month:04 pages:453-464 https://dx.doi.org/10.1039/c7pp00392g lizenzpflichtig Volltext GBV_USEFLAG_A SYSFLAG_A GBV_SPRINGER GBV_ILN_24 GBV_ILN_32 GBV_ILN_62 GBV_ILN_69 GBV_ILN_74 GBV_ILN_120 GBV_ILN_170 GBV_ILN_374 GBV_ILN_702 GBV_ILN_2020 GBV_ILN_2021 GBV_ILN_2026 GBV_ILN_2027 GBV_ILN_2110 GBV_ILN_2190 GBV_ILN_4035 GBV_ILN_4037 GBV_ILN_4112 GBV_ILN_4305 35.16 ASE 42.14 ASE AR 17 2018 4 04 453-464
language	English
source	Enthalten in Photochemical & photobiological sciences 17(2018), 4 vom: Apr., Seite 453-464 volume:17 year:2018 number:4 month:04 pages:453-464
sourceStr	Enthalten in Photochemical & photobiological sciences 17(2018), 4 vom: Apr., Seite 453-464 volume:17 year:2018 number:4 month:04 pages:453-464
format_phy_str_mv	Article
institution	findex.gbv.de
dewey-raw	620
isfreeaccess_bool	false
container_title	Photochemical & photobiological sciences
authorswithroles_txt_mv	Siddlingeshwar, B. @@aut@@ Kirilova, Elena M. @@aut@@ Belyakov, Sergey V. @@aut@@ Divakar, Darshan Devang @@aut@@ Alkheraif, Abdulaziz Abdullah @@aut@@
publishDateDaySort_date	2018-04-01T00:00:00Z
hierarchy_top_id	342893742
dewey-sort	3620
id	SPR043731139
language_de	englisch
fullrecord	<?xml version="1.0" encoding="UTF-8"?><collection xmlns="http://www.loc.gov/MARC21/slim"><record><leader>01000caa a22002652 4500</leader><controlfield tag="001">SPR043731139</controlfield><controlfield tag="003">DE-627</controlfield><controlfield tag="005">20220112055016.0</controlfield><controlfield tag="007">cr uuu---uuuuu</controlfield><controlfield tag="008">210409s2018 xx \|\|\|\|\|o 00\| \|\|eng c</controlfield><datafield tag="024" ind1="7" ind2=" "><subfield code="a">10.1039/c7pp00392g</subfield><subfield code="2">doi</subfield></datafield><datafield tag="035" ind1=" " ind2=" "><subfield code="a">(DE-627)SPR043731139</subfield></datafield><datafield tag="035" ind1=" " ind2=" "><subfield code="a">(DE-599)SPRc7pp00392g-e</subfield></datafield><datafield tag="035" ind1=" " ind2=" "><subfield code="a">(SPR)c7pp00392g-e</subfield></datafield><datafield tag="040" ind1=" " ind2=" "><subfield code="a">DE-627</subfield><subfield code="b">ger</subfield><subfield code="c">DE-627</subfield><subfield code="e">rakwb</subfield></datafield><datafield tag="041" ind1=" " ind2=" "><subfield code="a">eng</subfield></datafield><datafield tag="082" ind1="0" ind2="4"><subfield code="a">620</subfield><subfield code="q">ASE</subfield></datafield><datafield tag="084" ind1=" " ind2=" "><subfield code="a">35.16</subfield><subfield code="2">bkl</subfield></datafield><datafield tag="084" ind1=" " ind2=" "><subfield code="a">42.14</subfield><subfield code="2">bkl</subfield></datafield><datafield tag="100" ind1="1" ind2=" "><subfield code="a">Siddlingeshwar, B.</subfield><subfield code="e">verfasserin</subfield><subfield code="4">aut</subfield></datafield><datafield tag="245" ind1="1" ind2="0"><subfield code="a">Photophysical properties of benzanthrone derivatives: effect of substituent, solvent polarity and hydrogen bonding</subfield></datafield><datafield tag="264" ind1=" " ind2="1"><subfield code="c">2018</subfield></datafield><datafield tag="336" ind1=" " ind2=" "><subfield code="a">Text</subfield><subfield code="b">txt</subfield><subfield code="2">rdacontent</subfield></datafield><datafield tag="337" ind1=" " ind2=" "><subfield code="a">Computermedien</subfield><subfield code="b">c</subfield><subfield code="2">rdamedia</subfield></datafield><datafield tag="338" ind1=" " ind2=" "><subfield code="a">Online-Ressource</subfield><subfield code="b">cr</subfield><subfield code="2">rdacarrier</subfield></datafield><datafield tag="520" ind1=" " ind2=" "><subfield code="a">Abstract Benzanthrone derivatives are potential fluorescent probes for various chemical and biological environments. A mechanistic understanding of their photophysical properties is pivotal for designing an efficient fluorescence sensor based on the benzanthrone framework. In this study, we report on the effect of chemical substitution on the photophysical properties of two benzanthrone derivatives, namely, 3-(N′-methyl)-piperazino-7H-benzo[de]anthracen-7-one [Me-PBA] and 3-(N′-phenyl)-piperazino-7H-benzo[de]anthracen-7-one [Ph-PBA] in different solvents and solvent mixtures of varying polarities and proticities. Both benzanthrone derivatives show interesting solvent-dependent photophysical properties. Although both derivatives exhibit strong intramolecular charge transfer (ICT) characteristics in the excited state, the extent of the charge transfer is significantly influenced by the nature of the chemical substitution. Modulation of photophysical parameters as a function of solvent properties led us to propose that ICT is affected by solvent polarity and hydrogen bonding. From the viscosity effect, it is revealed that the weaker emission of Ph-PBA compared to Me-PBA in polar solvents is primarily due to the non-radiative torsional motion of the phenyl group in the former derivative. In protic solvents, intermolecular hydrogen bonding imparts strong non-radiative deactivation to both derivatives, thus rendering a weak fluorescence yield.</subfield></datafield><datafield tag="700" ind1="1" ind2=" "><subfield code="a">Kirilova, Elena M.</subfield><subfield code="e">verfasserin</subfield><subfield code="4">aut</subfield></datafield><datafield tag="700" ind1="1" ind2=" "><subfield code="a">Belyakov, Sergey V.</subfield><subfield code="e">verfasserin</subfield><subfield code="4">aut</subfield></datafield><datafield tag="700" ind1="1" ind2=" "><subfield code="a">Divakar, Darshan Devang</subfield><subfield code="e">verfasserin</subfield><subfield code="4">aut</subfield></datafield><datafield tag="700" ind1="1" ind2=" "><subfield code="a">Alkheraif, Abdulaziz Abdullah</subfield><subfield code="e">verfasserin</subfield><subfield code="4">aut</subfield></datafield><datafield tag="773" ind1="0" ind2="8"><subfield code="i">Enthalten in</subfield><subfield code="t">Photochemical & photobiological sciences</subfield><subfield code="d">Heidelberg : Springer, 2002</subfield><subfield code="g">17(2018), 4 vom: Apr., Seite 453-464</subfield><subfield code="w">(DE-627)342893742</subfield><subfield code="w">(DE-600)2072584-X</subfield><subfield code="x">1474-9092</subfield><subfield code="7">nnns</subfield></datafield><datafield tag="773" ind1="1" ind2="8"><subfield code="g">volume:17</subfield><subfield code="g">year:2018</subfield><subfield code="g">number:4</subfield><subfield code="g">month:04</subfield><subfield code="g">pages:453-464</subfield></datafield><datafield tag="856" ind1="4" ind2="0"><subfield code="u">https://dx.doi.org/10.1039/c7pp00392g</subfield><subfield code="z">lizenzpflichtig</subfield><subfield code="3">Volltext</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_USEFLAG_A</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">SYSFLAG_A</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_SPRINGER</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_24</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_32</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_62</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_69</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_74</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_120</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_170</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_374</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_702</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_2020</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_2021</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_2026</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_2027</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_2110</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_2190</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_4035</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_4037</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_4112</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_4305</subfield></datafield><datafield tag="936" ind1="b" ind2="k"><subfield code="a">35.16</subfield><subfield code="q">ASE</subfield></datafield><datafield tag="936" ind1="b" ind2="k"><subfield code="a">42.14</subfield><subfield code="q">ASE</subfield></datafield><datafield tag="951" ind1=" " ind2=" "><subfield code="a">AR</subfield></datafield><datafield tag="952" ind1=" " ind2=" "><subfield code="d">17</subfield><subfield code="j">2018</subfield><subfield code="e">4</subfield><subfield code="c">04</subfield><subfield code="h">453-464</subfield></datafield></record></collection>
author	Siddlingeshwar, B.
spellingShingle	Siddlingeshwar, B. ddc 620 bkl 35.16 bkl 42.14 Photophysical properties of benzanthrone derivatives: effect of substituent, solvent polarity and hydrogen bonding
authorStr	Siddlingeshwar, B.
ppnlink_with_tag_str_mv	@@773@@(DE-627)342893742
format	electronic Article
dewey-ones	620 - Engineering & allied operations
delete_txt_mv	keep
author_role	aut aut aut aut aut
collection	springer
remote_str	true
illustrated	Not Illustrated
issn	1474-9092
topic_title	620 ASE 35.16 bkl 42.14 bkl Photophysical properties of benzanthrone derivatives: effect of substituent, solvent polarity and hydrogen bonding
topic	ddc 620 bkl 35.16 bkl 42.14
topic_unstemmed	ddc 620 bkl 35.16 bkl 42.14
topic_browse	ddc 620 bkl 35.16 bkl 42.14
format_facet	Elektronische Aufsätze Aufsätze Elektronische Ressource
format_main_str_mv	Text Zeitschrift/Artikel
carriertype_str_mv	cr
hierarchy_parent_title	Photochemical & photobiological sciences
hierarchy_parent_id	342893742
dewey-tens	620 - Engineering
hierarchy_top_title	Photochemical & photobiological sciences
isfreeaccess_txt	false
familylinks_str_mv	(DE-627)342893742 (DE-600)2072584-X
title	Photophysical properties of benzanthrone derivatives: effect of substituent, solvent polarity and hydrogen bonding
ctrlnum	(DE-627)SPR043731139 (DE-599)SPRc7pp00392g-e (SPR)c7pp00392g-e
title_full	Photophysical properties of benzanthrone derivatives: effect of substituent, solvent polarity and hydrogen bonding
author_sort	Siddlingeshwar, B.
journal	Photochemical & photobiological sciences
journalStr	Photochemical & photobiological sciences
lang_code	eng
isOA_bool	false
dewey-hundreds	600 - Technology
recordtype	marc
publishDateSort	2018
contenttype_str_mv	txt
container_start_page	453
author_browse	Siddlingeshwar, B. Kirilova, Elena M. Belyakov, Sergey V. Divakar, Darshan Devang Alkheraif, Abdulaziz Abdullah
container_volume	17
class	620 ASE 35.16 bkl 42.14 bkl
format_se	Elektronische Aufsätze
author-letter	Siddlingeshwar, B.
doi_str_mv	10.1039/c7pp00392g
dewey-full	620
author2-role	verfasserin
title_sort	photophysical properties of benzanthrone derivatives: effect of substituent, solvent polarity and hydrogen bonding
title_auth	Photophysical properties of benzanthrone derivatives: effect of substituent, solvent polarity and hydrogen bonding
abstract	Abstract Benzanthrone derivatives are potential fluorescent probes for various chemical and biological environments. A mechanistic understanding of their photophysical properties is pivotal for designing an efficient fluorescence sensor based on the benzanthrone framework. In this study, we report on the effect of chemical substitution on the photophysical properties of two benzanthrone derivatives, namely, 3-(N′-methyl)-piperazino-7H-benzo[de]anthracen-7-one [Me-PBA] and 3-(N′-phenyl)-piperazino-7H-benzo[de]anthracen-7-one [Ph-PBA] in different solvents and solvent mixtures of varying polarities and proticities. Both benzanthrone derivatives show interesting solvent-dependent photophysical properties. Although both derivatives exhibit strong intramolecular charge transfer (ICT) characteristics in the excited state, the extent of the charge transfer is significantly influenced by the nature of the chemical substitution. Modulation of photophysical parameters as a function of solvent properties led us to propose that ICT is affected by solvent polarity and hydrogen bonding. From the viscosity effect, it is revealed that the weaker emission of Ph-PBA compared to Me-PBA in polar solvents is primarily due to the non-radiative torsional motion of the phenyl group in the former derivative. In protic solvents, intermolecular hydrogen bonding imparts strong non-radiative deactivation to both derivatives, thus rendering a weak fluorescence yield.
abstractGer	Abstract Benzanthrone derivatives are potential fluorescent probes for various chemical and biological environments. A mechanistic understanding of their photophysical properties is pivotal for designing an efficient fluorescence sensor based on the benzanthrone framework. In this study, we report on the effect of chemical substitution on the photophysical properties of two benzanthrone derivatives, namely, 3-(N′-methyl)-piperazino-7H-benzo[de]anthracen-7-one [Me-PBA] and 3-(N′-phenyl)-piperazino-7H-benzo[de]anthracen-7-one [Ph-PBA] in different solvents and solvent mixtures of varying polarities and proticities. Both benzanthrone derivatives show interesting solvent-dependent photophysical properties. Although both derivatives exhibit strong intramolecular charge transfer (ICT) characteristics in the excited state, the extent of the charge transfer is significantly influenced by the nature of the chemical substitution. Modulation of photophysical parameters as a function of solvent properties led us to propose that ICT is affected by solvent polarity and hydrogen bonding. From the viscosity effect, it is revealed that the weaker emission of Ph-PBA compared to Me-PBA in polar solvents is primarily due to the non-radiative torsional motion of the phenyl group in the former derivative. In protic solvents, intermolecular hydrogen bonding imparts strong non-radiative deactivation to both derivatives, thus rendering a weak fluorescence yield.
abstract_unstemmed	Abstract Benzanthrone derivatives are potential fluorescent probes for various chemical and biological environments. A mechanistic understanding of their photophysical properties is pivotal for designing an efficient fluorescence sensor based on the benzanthrone framework. In this study, we report on the effect of chemical substitution on the photophysical properties of two benzanthrone derivatives, namely, 3-(N′-methyl)-piperazino-7H-benzo[de]anthracen-7-one [Me-PBA] and 3-(N′-phenyl)-piperazino-7H-benzo[de]anthracen-7-one [Ph-PBA] in different solvents and solvent mixtures of varying polarities and proticities. Both benzanthrone derivatives show interesting solvent-dependent photophysical properties. Although both derivatives exhibit strong intramolecular charge transfer (ICT) characteristics in the excited state, the extent of the charge transfer is significantly influenced by the nature of the chemical substitution. Modulation of photophysical parameters as a function of solvent properties led us to propose that ICT is affected by solvent polarity and hydrogen bonding. From the viscosity effect, it is revealed that the weaker emission of Ph-PBA compared to Me-PBA in polar solvents is primarily due to the non-radiative torsional motion of the phenyl group in the former derivative. In protic solvents, intermolecular hydrogen bonding imparts strong non-radiative deactivation to both derivatives, thus rendering a weak fluorescence yield.
collection_details	GBV_USEFLAG_A SYSFLAG_A GBV_SPRINGER GBV_ILN_24 GBV_ILN_32 GBV_ILN_62 GBV_ILN_69 GBV_ILN_74 GBV_ILN_120 GBV_ILN_170 GBV_ILN_374 GBV_ILN_702 GBV_ILN_2020 GBV_ILN_2021 GBV_ILN_2026 GBV_ILN_2027 GBV_ILN_2110 GBV_ILN_2190 GBV_ILN_4035 GBV_ILN_4037 GBV_ILN_4112 GBV_ILN_4305
container_issue	4
title_short	Photophysical properties of benzanthrone derivatives: effect of substituent, solvent polarity and hydrogen bonding
url	https://dx.doi.org/10.1039/c7pp00392g
remote_bool	true
author2	Kirilova, Elena M. Belyakov, Sergey V. Divakar, Darshan Devang Alkheraif, Abdulaziz Abdullah
author2Str	Kirilova, Elena M. Belyakov, Sergey V. Divakar, Darshan Devang Alkheraif, Abdulaziz Abdullah
ppnlink	342893742
mediatype_str_mv	c
isOA_txt	false
hochschulschrift_bool	false
doi_str	10.1039/c7pp00392g
up_date	2024-07-03T20:30:55.190Z
_version_	1803591252907655168
fullrecord_marcxml	<?xml version="1.0" encoding="UTF-8"?><collection xmlns="http://www.loc.gov/MARC21/slim"><record><leader>01000caa a22002652 4500</leader><controlfield tag="001">SPR043731139</controlfield><controlfield tag="003">DE-627</controlfield><controlfield tag="005">20220112055016.0</controlfield><controlfield tag="007">cr uuu---uuuuu</controlfield><controlfield tag="008">210409s2018 xx \|\|\|\|\|o 00\| \|\|eng c</controlfield><datafield tag="024" ind1="7" ind2=" "><subfield code="a">10.1039/c7pp00392g</subfield><subfield code="2">doi</subfield></datafield><datafield tag="035" ind1=" " ind2=" "><subfield code="a">(DE-627)SPR043731139</subfield></datafield><datafield tag="035" ind1=" " ind2=" "><subfield code="a">(DE-599)SPRc7pp00392g-e</subfield></datafield><datafield tag="035" ind1=" " ind2=" "><subfield code="a">(SPR)c7pp00392g-e</subfield></datafield><datafield tag="040" ind1=" " ind2=" "><subfield code="a">DE-627</subfield><subfield code="b">ger</subfield><subfield code="c">DE-627</subfield><subfield code="e">rakwb</subfield></datafield><datafield tag="041" ind1=" " ind2=" "><subfield code="a">eng</subfield></datafield><datafield tag="082" ind1="0" ind2="4"><subfield code="a">620</subfield><subfield code="q">ASE</subfield></datafield><datafield tag="084" ind1=" " ind2=" "><subfield code="a">35.16</subfield><subfield code="2">bkl</subfield></datafield><datafield tag="084" ind1=" " ind2=" "><subfield code="a">42.14</subfield><subfield code="2">bkl</subfield></datafield><datafield tag="100" ind1="1" ind2=" "><subfield code="a">Siddlingeshwar, B.</subfield><subfield code="e">verfasserin</subfield><subfield code="4">aut</subfield></datafield><datafield tag="245" ind1="1" ind2="0"><subfield code="a">Photophysical properties of benzanthrone derivatives: effect of substituent, solvent polarity and hydrogen bonding</subfield></datafield><datafield tag="264" ind1=" " ind2="1"><subfield code="c">2018</subfield></datafield><datafield tag="336" ind1=" " ind2=" "><subfield code="a">Text</subfield><subfield code="b">txt</subfield><subfield code="2">rdacontent</subfield></datafield><datafield tag="337" ind1=" " ind2=" "><subfield code="a">Computermedien</subfield><subfield code="b">c</subfield><subfield code="2">rdamedia</subfield></datafield><datafield tag="338" ind1=" " ind2=" "><subfield code="a">Online-Ressource</subfield><subfield code="b">cr</subfield><subfield code="2">rdacarrier</subfield></datafield><datafield tag="520" ind1=" " ind2=" "><subfield code="a">Abstract Benzanthrone derivatives are potential fluorescent probes for various chemical and biological environments. A mechanistic understanding of their photophysical properties is pivotal for designing an efficient fluorescence sensor based on the benzanthrone framework. In this study, we report on the effect of chemical substitution on the photophysical properties of two benzanthrone derivatives, namely, 3-(N′-methyl)-piperazino-7H-benzo[de]anthracen-7-one [Me-PBA] and 3-(N′-phenyl)-piperazino-7H-benzo[de]anthracen-7-one [Ph-PBA] in different solvents and solvent mixtures of varying polarities and proticities. Both benzanthrone derivatives show interesting solvent-dependent photophysical properties. Although both derivatives exhibit strong intramolecular charge transfer (ICT) characteristics in the excited state, the extent of the charge transfer is significantly influenced by the nature of the chemical substitution. Modulation of photophysical parameters as a function of solvent properties led us to propose that ICT is affected by solvent polarity and hydrogen bonding. From the viscosity effect, it is revealed that the weaker emission of Ph-PBA compared to Me-PBA in polar solvents is primarily due to the non-radiative torsional motion of the phenyl group in the former derivative. In protic solvents, intermolecular hydrogen bonding imparts strong non-radiative deactivation to both derivatives, thus rendering a weak fluorescence yield.</subfield></datafield><datafield tag="700" ind1="1" ind2=" "><subfield code="a">Kirilova, Elena M.</subfield><subfield code="e">verfasserin</subfield><subfield code="4">aut</subfield></datafield><datafield tag="700" ind1="1" ind2=" "><subfield code="a">Belyakov, Sergey V.</subfield><subfield code="e">verfasserin</subfield><subfield code="4">aut</subfield></datafield><datafield tag="700" ind1="1" ind2=" "><subfield code="a">Divakar, Darshan Devang</subfield><subfield code="e">verfasserin</subfield><subfield code="4">aut</subfield></datafield><datafield tag="700" ind1="1" ind2=" "><subfield code="a">Alkheraif, Abdulaziz Abdullah</subfield><subfield code="e">verfasserin</subfield><subfield code="4">aut</subfield></datafield><datafield tag="773" ind1="0" ind2="8"><subfield code="i">Enthalten in</subfield><subfield code="t">Photochemical & photobiological sciences</subfield><subfield code="d">Heidelberg : Springer, 2002</subfield><subfield code="g">17(2018), 4 vom: Apr., Seite 453-464</subfield><subfield code="w">(DE-627)342893742</subfield><subfield code="w">(DE-600)2072584-X</subfield><subfield code="x">1474-9092</subfield><subfield code="7">nnns</subfield></datafield><datafield tag="773" ind1="1" ind2="8"><subfield code="g">volume:17</subfield><subfield code="g">year:2018</subfield><subfield code="g">number:4</subfield><subfield code="g">month:04</subfield><subfield code="g">pages:453-464</subfield></datafield><datafield tag="856" ind1="4" ind2="0"><subfield code="u">https://dx.doi.org/10.1039/c7pp00392g</subfield><subfield code="z">lizenzpflichtig</subfield><subfield code="3">Volltext</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_USEFLAG_A</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">SYSFLAG_A</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_SPRINGER</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_24</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_32</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_62</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_69</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_74</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_120</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_170</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_374</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_702</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_2020</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_2021</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_2026</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_2027</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_2110</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_2190</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_4035</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_4037</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_4112</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_ILN_4305</subfield></datafield><datafield tag="936" ind1="b" ind2="k"><subfield code="a">35.16</subfield><subfield code="q">ASE</subfield></datafield><datafield tag="936" ind1="b" ind2="k"><subfield code="a">42.14</subfield><subfield code="q">ASE</subfield></datafield><datafield tag="951" ind1=" " ind2=" "><subfield code="a">AR</subfield></datafield><datafield tag="952" ind1=" " ind2=" "><subfield code="d">17</subfield><subfield code="j">2018</subfield><subfield code="e">4</subfield><subfield code="c">04</subfield><subfield code="h">453-464</subfield></datafield></record></collection>
score	7.4028063

Nicht das Richtige dabei?

Schreiben Sie uns!

Photophysical properties of benzanthrone derivatives: effect of substituent, solvent polarity and hydrogen bonding

Nicht das Richtige dabei?

Zugang & Verfügbarkeit

Vorhandene Bände

Nicht das Richtige dabei?